Photoresist composition including a chrysene compound, method of forming a pattern using the same, and method of fabricating 6-nitrochrysene

Abstract

A photoresist composition, a method of forming a pattern, and a method of synthesizing 6-nitrochrysene, the photoresist composition includes a polymer resin; a photo acid generator; a quencher; an organic solvent; and an etching resistance enhancer, wherein the etching resistance enhancer is represented by the following Chemical Formula 1,

What is claimed is: 
     
         1 . A photoresist composition, comprising:
 a polymer resin;   a photo acid generator;   a quencher;   an organic solvent; and   an etching resistance enhancer,   wherein:   the etching resistance enhancer is represented by the following Chemical Formula 1,   
       
         
           
           
               
               
           
         
         in Chemical Formula 1, R is a nitro group, a nitrile group, a trifluoromethyl group, an acetate group, or a triisopropylsilyl group. 
       
     
     
         2 . The photoresist composition as claimed in  claim 1 , wherein:
 R is a nitro group, and   the etching resistance enhancer is represented by the following Chemical Formula 2,   
       
         
           
           
               
               
           
         
       
     
     
         3 . The photoresist composition as claimed in  claim 1 , wherein the photoresist composition includes the etching resistance enhancer in an amount of 0.1 wt % to 1 wt %, based on a total weight of the photoresist composition. 
     
     
         4 . The photoresist composition as claimed in  claim 3 , wherein the photoresist composition includes:
 3 wt % to 20 wt % of the polymer resin,   0.5 wt % to 10 wt % of the photo acid generator,   0.1 wt % to 5 wt % of the quencher, and   64 wt % to 96.3 wt % of the organic solvent, all wt % being based on the total weight of the photoresist composition.   
     
     
         5 . The photoresist composition as claimed in  claim 1 , wherein the polymer resin includes polymethylmethacrylate, poly(t-butylmethacrylate), poly(methacrylic acid), or poly(norbornylmethacrylate). 
     
     
         6 . The photoresist composition as claimed in  claim 1 , wherein the photo acid generator includes an aryldiazonium salt, a diaryliodonium salt, a triarylsulfonium salt, a triarylphosphonium salt, a carboxylic acid, a sulfonic acid, a phosphoric acid, or a hydrogen halide. 
     
     
         7 . The photoresist composition as claimed in  claim 1 , wherein the quencher includes hydrogen chloride, an ethyl ester, an alcohol, water, a fluorine compound, a cyanide compound, a ketone compound, a bromide compound, an iodide compound, an amine compound, an aldehyde compound, a phenol compound, a nitro compound, or a triarylsulfonium salt. 
     
     
         8 . The photoresist composition as claimed in  claim 1 , wherein the organic solvent includes propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 2-hydroxyisobutyric acid methyl ester, ethyl lactate, ethyl lactate, cyclohexanone, heptanone, or lactone. 
     
     
         9 . A method of forming a pattern, the method comprising:
 forming an etching target layer on a substrate;   coating the etching target layer with a photoresist composition to form a photoresist layer;   performing an exposure process on the photoresist layer;   performing a developing process on the photoresist layer to form a photoresist pattern; and   etching the etching target layer using the photoresist pattern as an etch mask to form a mask pattern,   wherein:   the photoresist composition includes:
 a polymer resin; 
 a photo acid generator; 
 a quencher; 
 an organic solvent; and 
 an etching resistance enhancer, and 
   the etching resistance enhancer is represented by the following Chemical Formula 1,   
       
         
           
           
               
               
           
         
         in Chemical Formula 1, R is a nitro group, a nitrile group, a trifluoromethyl group, an acetate group, or a triisopropylsilyl group. 
       
     
     
         10 . The method as claimed in  claim 9 , wherein the etching resistance enhancer represented by Chemical Formula 1 is represented by the following Chemical Formula 2, 
       
         
           
           
               
               
           
         
       
     
     
         11 . A method of synthesizing 6-nitrochrysene, the method comprising:
 dissolving 1-(chloromethyl)naphthalene in a first solvent to prepare a first solution, adding triphenylphosphine into the first solution, and stirring the first solution to obtain a first product;   filtering the first product and washing the first product with a first detergent;   dissolving the first product in a second solvent to prepare a second solution, and adding tetrabutylammoniumhydroxide and benzaldehyde into the second solution and stirring the second solution to obtain a second product;   separating and purifying the second product using a column chromatography;   dissolving the second product in a third solvent to prepare a third solution, and adding iodine into the third solution and irradiating ultraviolet rays to the third solution while stirring the third solution;   removing iodine from the third solution by using an aqueous sodium thiosulfate solution and performing a first extraction process by using water and toluene to obtain a first organic layer;   removing toluene from the first organic layer and washing the first organic layer using a second detergent to obtain a third product;   dissolving the third product in a fourth solvent to prepare a fourth solution; and   adding a nitric acid solution into the fourth solution and reacting the third product with the nitric acid solution.   
     
     
         12 . The method as claimed in  claim 11 , wherein:
 the first solvent is toluene, and   the first detergent is diethyl ether.   
     
     
         13 . The method as claimed in  claim 11 , wherein:
 the second solvent is dichloromethane, and   the third solvent is toluene.   
     
     
         14 . The method as claimed in  claim 11 , further comprising:
 adding sodium bicarbonate aqueous solution into the fourth solution to neutralize the fourth solution, and performing a second extraction process using water and dichloromethane to obtain a second organic layer; and   separating and purifying the second organic layer using a column chromatography and washing the second organic layer.   
     
     
         15 . The method as claimed in  claim 14 , wherein the fourth solvent is dichloromethane. 
     
     
         16 . The method as claimed in  claim 11 , wherein stirring the first solution to obtain a first product is carried out at 100° C. to 120° C. for 10 hours to 14 hours. 
     
     
         17 . The method as claimed in  claim 11 , wherein the 1-(chloromethyl)naphthalene and the triphenylphosphine are added into the first solution in a molar ratio of 1:3. 
     
     
         18 . The method as claimed in  claim 11 , wherein the stirring the second solution to obtain a second product is carried out at 10 to 40° C. for 10 to 14 hours. 
     
     
         19 . The method as claimed in  claim 11 , wherein the stirring the third solution is carried out for 20 to 28 hours. 
     
     
         20 . The method as claimed in  claim 11 , wherein:
 the first product is   
       
         
           
           
               
               
           
         
         the second product is 
       
       
         
           
           
               
               
           
         
       
       and
 the third product is chrysene.